The first sheriff of Lewis County was Chilton B. Tate who was appointed by Governor Dunklin in 1833. Sheriff Tate was elected later that year with 158 votes and remained Sheriff until 1838. He was elected state representative and remained in that position until 1842 when he returned to Lewis County and was reelected to the position of Sheriff. He died in 1879.   

Sheriff Tate presented the first criminal matter to a Lewis County Grand Jury in 1834. In a rather audacious beginning, a woman, Elizabeth Jones, (wife of Benjamin Jones), was indicted for adultery along with a co-defendant Joseph Fry. According to local records the matter was partially tried and then dismissed. The first ever civil action tried before a jury of four men was Thomas Creasey v. Fountain Jones. The jury sided with plaintiff Creasey and awarded him $2.10 to be paid by Mr. Jones.

The first ever courthouse in Monticello was a small log structure built by J.B. Buckley in 1834 for the sum of $210. The county had to borrow $100 to pay the total amount. Recognizing the need for a larger building the second courthouse was built in 1839 for the sum of $3,200. In 1875, the current courthouse was built by McAlister and Company for the sum of $9,750. Court has been held in Monticello since 1834. 

The first jail was built near the courthouse in 1842 at a cost of $1,000 under the guidance of Sheriff Tate. The jail and sheriff’s house have remained at the county seat since that time. At some point the jail and sheriff's house were combined. This required the sheriff and his wife to care for the prisoners. The Sheriff's wife generally provided the meals for her family and the prisoners as well. 

Sheriff George W. Smith, occupied the house and jail, along with his family in the 1920s. Besides raising a family, Sheriff Smith executed search warrants on illegal whiskey stills throughout Lewis County during Prohibition. The language in his affidavit remains much the same as it is today for illegal drugs. His son, Burrell Smith, who still resides in Monticello, has fond memories of living there. 

The latest edition, built in 1941, included the jail, which was located on the second floor, and the sheriff's living quarters which were on the first floor. Sheriff Alexander Fife Stephenson and his family were the first to occupy the residence and jail. Sheriff Stephenson, who was first elected in 1932, informed his brother he was pursuing the position because, 'the price of hogs was less than four cents a pound' among other concerns. His daughter, Mary McReynolds, who still resides in Lewis County today, recalls being lifted up into the jail to play checkers with a prisoner and also has fond memories of living there.

Sheriff Pearl Hicks, who was appointed in October 1962, after Sheriff Wilbur Wallace had died in a vehicle crash, and was then elected in November 1962, remains the longest serving sheriff in Lewis County history. He served from 1962 to the time of his retirement in 1979. 

While the Sheriff's house and jail built in 1941 still stands, it has been remodeled and serves as office space. In 1996, Lewis County citizens approved the addition of an 18 bed facility to the current structure. This new jail included a kitchen, booking room, holding cell, control room, property room, two inmate pods and an outdoor recreation area. 

The Sheriff's Office remains a full service operation and after serving the public for 182 years, looks forward to many more.